England Under-21s' final scheduled fixture before Euro 2019 ended in a 2-1 defeat after Germany claimed a dramatic injury-time winner at the Vitality Stadium.
With senior manager Gareth Southgate watching from the stands, England looked to have done enough to earn a draw after stand-in captain Dominic Solanke cancelled out Mahmoud Dahoud's opener.
But Germany defender Felix Uduokhai fired home a minute into added time to halt the Young Lions' 18-match unbeaten run.
Under-21 boss Aidy Boothroyd, whose team begin their European Championship campaign on June 18 against France in Cesena, made nine changes from last week's 1-1 draw with Poland.
Phil Foden and Kieran Dowell were the only players retained, while Ryan Sessegnon, Demarai Gray and Harvey Barnes were among those brought in.
With Southgate back from Montenegro in time to attend and places in Boothroyd's summer squad at stake, those selected had major incentives to impress.
They initially struggled to do so and deservedly fell behind with 27 minutes played. Arne Maier played a lofted pass to the edge of the penalty area where Borussia Dortmund midfielder Dahoud chested down to rifle a low shot beyond Dean Henderson.
Germany, managed by Stefan Kuntz who scored against Southgate's England in the semi-finals of Euro 96, had earlier threatened through Benjamin Henrichs and Florian Neuhaus, while Henderson had to be alert to deny Luca Waldschmidt a simple tap-in.
Freiburg forward Waldschmidt almost doubled the advantage when superb build-up play culminated in him striking the right post, with Nadiem Amiri unable to turn home the rebound.
Aside from the incessant sound of the England band, there was a relatively subdued atmosphere on the south coast, not helped by the hosts' lack of attacking threat.
Lone striker Solanke, skippering the side on his club ground and watched from the stands by Bournemouth team-mate Callum Wilson, cut an isolated figure and was forced to feed off scraps until he levelled two minutes before the break.
Manchester City teenager Foden foraged on the edge of the box before Maier's attempted clearance ricocheted kindly for Solanke to sidestep goalkeeper Florian Muller and slot into the empty net.
The unmerited equaliser appeared to spark life into England and Dowell, Barnes and the energetic Foden were each narrowly off target from distance early in the second period.
A flurry of second-half substitutions did not help the flow of the contest, with Boothroyd making six alterations to Kuntz's seven.
England's only two defeats in the last two years came against Germany, including a semi-final penalty shoot-out loss at Euro 2017.
And they were to suffer further disappointment at the hands of the visitors.
With Kyle Walker-Peters lying injured in the box, Uduokhai controlled Henrichs' left-wing cross to fire home from close range via a deflection.